Preparation of beta-hydroxyesters from isoxazolines. A selective Ni(0)bpy-catalyzed electrochemical method

An elect rocatalytic method for the reductive N-O cleavage of isoxazolines is described. Ni(0)bpy, generated in situ, was used to promote selective ring opening of 3-methoxy-5-phenylisoxazoline (1a) and 3-methoxy-[4,5]cyclohexylisoxazoline (1b). DMF and NaI were used as solvent and supporting electr...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 45; pp. 8217 - 8220
Main Authors Caetano, VF, Demnitz, FWJ, Diniz, FB, Mariz, RM, Navarro, M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 03.11.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ROUTE
KETONES
1,3-DIPOLAR CYCLOADDITIONS
2-ISOXAZOLINES
REDUCTION
CONVERSION
NITRILE OXIDES
ESTERS
DERIVATIVES
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Summary:An elect rocatalytic method for the reductive N-O cleavage of isoxazolines is described. Ni(0)bpy, generated in situ, was used to promote selective ring opening of 3-methoxy-5-phenylisoxazoline (1a) and 3-methoxy-[4,5]cyclohexylisoxazoline (1b). DMF and NaI were used as solvent and supporting electrolyte, and (3-hydroxyesters 2a and 26 were obtained in high yields respectively, after acid hydrolysis. (beta-Hydroxynitriles 3a and 3b were also identified as side products. (C) 2003 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2003.09.081